$119+ Cheap flights from Vermont to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Oct 10 — Oct 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Vermont to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Vermont to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Vermont to ChicagoExplore the most affordable flight options available from Vermont to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
Explore the most affordable flight options available from Vermont to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This Trip.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:16 pm -
1 stop17h 35m
Thu 10/226:58 pm -
1 stop18h 23m
Deal found 9/6![Frontier logo]()
$277
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:23 pm -
Nonstop2h 52m
Fri 10/97:52 pm -
Nonstop2h 21m
Deal found 9/8![American Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:15 pm -
Nonstop2h 10m
Sat 10/174:20 pm -
Nonstop2h 00m
Deal found 9/8![Southwest logo]()
$282
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:25 am -
1 stop5h 59m
Mon 10/262:42 pm -
1 stop8h 17m
Deal found 9/9![JetBlue logo]()
$283
This Booking.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:16 pm -
1 stop8h 43m
Sun 10/43:50 pm -
1 stop21h 28m
Deal found 9/9![Frontier logo]()
$284
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:25 am -
1 stop4h 33m
Tue 10/63:00 pm -
1 stop7h 14m
Deal found 9/9![JetBlue logo]()
$285
This KAYAK deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:25 am -
1 stop4h 33m
Tue 9/293:00 pm -
1 stop7h 14m
Deal found 9/7![JetBlue logo]()
$287
This Priceline deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:16 pm -
1 stop8h 43m
Fri 9/253:00 pm -
1 stop7h 14m
Deal found 9/5![Multiple Airlines logo]()
$288
This JetBlue deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:25 am -
1 stop5h 59m
Tue 10/202:55 pm -
1 stop8h 03m
Deal found 9/7![JetBlue logo]()
$289
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:05 am -
1 stop6h 02m
Thu 10/158:39 pm -
Nonstop2h 20m
Deal found 9/9![American Airlines logo]()
$292
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:50 am -
Nonstop2h 20m
Mon 11/166:00 am -
1 stop5h 10m
Deal found 9/8![Southwest logo]()
$292
This Flightnetwork deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:13 pm -
1 stop29h 46m
Fri 9/253:50 pm -
1 stop24h 28m
Deal found 9/9![Frontier logo]()
$292
Best flights from Vermont to ChicagoDiscover carefully curated flight deals from Vermont to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from Vermont to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
1 stop6h 13m
Mon 12/1410:57 am -
Nonstop2h 11m
Deal found 9/9![United Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:55 am -
1 stop6h 25m
Sat 10/174:20 pm -
Nonstop2h 00m
Deal found 9/9![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/214:47 pm -
1 stop5h 43m
Tue 1/53:00 pm -
1 stop5h 10m
Deal found 9/9![Delta logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:32 pm -
2 stops20h 22m
Fri 10/307:56 pm -
1 stop12h 17m
Deal found 9/7![Multiple Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/257:25 am -
Nonstop2h 40m
Wed 1/278:25 am -
1 stop5h 40m
Deal found 9/8![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 am -
Nonstop2h 43m
Tue 10/2711:47 am -
Nonstop2h 14m
Deal found 9/9![United Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/72:22 pm -
1 stop7h 16m
Sun 11/86:15 am -
1 stop4h 24m
Deal found 9/9![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/256:00 am -
1 stop6h 40m
Wed 1/274:00 pm -
1 stop6h 52m
Deal found 9/8![United Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:50 am -
Nonstop2h 20m
Mon 10/57:50 am -
Nonstop2h 10m
Deal found 9/9![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:55 pm -
1 stop6h 05m
Tue 10/276:44 pm -
1 stop3h 39m
Deal found 9/5![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/43:16 pm -
1 stop19h 38m
Thu 10/89:40 am -
2 stops25h 39m
Deal found 9/8![Multiple Airlines logo]()
$378
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:13 pm -
Nonstop2h 37m
Mon 10/57:30 am -
Nonstop2h 09m
Deal found 9/8![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:50 pm -
1 stop5h 35m
Sun 10/187:05 pm -
Nonstop2h 00m
Deal found 9/9![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:30 am -
2 stops8h 17m
Sat 10/249:29 am -
1 stop5h 33m
Deal found 9/7![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:54 am -
Nonstop2h 51m
Tue 11/176:28 pm -
Nonstop2h 22m
Deal found 9/7![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:55 pm -
2 stops5h 55m
Wed 10/141:00 pm -
1 stop5h 15m
Deal found 9/9![Southwest logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:53 am -
2 stops23h 57m
Fri 10/237:56 pm -
1 stop12h 17m
Deal found 9/5![Multiple Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:50 am -
2 stops9h 38m
Sat 10/312:00 pm -
1 stop6h 07m
Deal found 9/7![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:37 am -
1 stop7h 23m
Mon 11/167:25 am -
Nonstop2h 18m
Deal found 9/9![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:15 pm -
Nonstop2h 10m
Mon 10/196:50 pm -
Nonstop2h 00m
Deal found 9/7![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
2 stops11h 37m
Tue 10/65:29 pm -
1 stop4h 54m
Deal found 9/6![Delta logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:16 pm -
1 stop17h 43m
Mon 10/510:44 am -
2 stops34h 49m
Deal found 9/8![Multiple Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
Nonstop2h 33m
Sat 10/102:30 pm -
Nonstop2h 12m
Deal found 9/5![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:15 pm -
Nonstop2h 10m
Mon 10/53:45 pm -
1 stop6h 40m
Deal found 9/5![Southwest logo]()
$337
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop6h 47m
Mon 11/166:28 pm -
Nonstop2h 22m
Deal found 9/6![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:00 am -
2 stops7h 59m
Mon 11/92:44 pm -
2 stops7h 22m
Deal found 9/9![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:30 am -
Nonstop2h 10m
Sat 10/174:50 pm -
1 stop3h 55m
Deal found 9/5![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:00 am -
1 stop13h 06m
Sun 10/2510:20 am -
2 stops23h 40m
Deal found 9/6![Multiple Airlines logo]()
$457
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:50 pm -
2 stops9h 25m
Sat 10/248:10 am -
Nonstop2h 05m
Deal found 9/6![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:00 am -
Nonstop2h 37m
Fri 10/26:12 pm -
1 stop4h 47m
Deal found 9/7![United Airlines logo]()
$349
Last-minute flights from Vermont to ChicagoDiscover last-minute flight deals from Vermont to Chicago. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Vermont to Chicago. Data last updated September 10, 2026 and is based on user searches.
This Flightnetwork deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:13 pm -
1 stop29h 46m
Fri 9/253:50 pm -
1 stop24h 28m
Deal found 9/9![Frontier logo]()
$292
This Priceline deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:16 pm -
1 stop8h 43m
Fri 9/253:00 pm -
1 stop7h 14m
Deal found 9/5![Multiple Airlines logo]()
$288
This KAYAK deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:25 am -
1 stop4h 33m
Tue 9/293:00 pm -
1 stop7h 14m
Deal found 9/7![JetBlue logo]()
$287
This Booking.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:16 pm -
1 stop8h 43m
Sun 10/43:50 pm -
1 stop21h 28m
Deal found 9/9![Frontier logo]()
$284
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:25 am -
1 stop4h 33m
Tue 10/63:00 pm -
1 stop7h 14m
Deal found 9/9![JetBlue logo]()
$285
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:23 pm -
Nonstop2h 52m
Fri 10/97:52 pm -
Nonstop2h 21m
Deal found 9/8![American Airlines logo]()
$282
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:05 am -
1 stop6h 02m
Thu 10/158:39 pm -
Nonstop2h 20m
Deal found 9/9![American Airlines logo]()
$292
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:00 pm -
1 stop5h 36m
Fri 10/164:50 pm -
1 stop5h 33m
Deal found 9/8![American Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:15 pm -
Nonstop2h 10m
Sat 10/174:20 pm -
Nonstop2h 00m
Deal found 9/8![Southwest logo]()
$282
This Trip.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:16 pm -
1 stop17h 35m
Thu 10/226:58 pm -
1 stop18h 23m
Deal found 9/6![Frontier logo]()
$277
This JetBlue deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:25 am -
1 stop5h 59m
Tue 10/202:55 pm -
1 stop8h 03m
Deal found 9/7![JetBlue logo]()
$289
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:25 am -
1 stop5h 59m
Mon 10/262:42 pm -
1 stop8h 17m
Deal found 9/9![JetBlue logo]()
$283
One-way flights from Vermont to ChicagoSearch for one-way flight options from Vermont to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Vermont to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:36 pm -
Nonstop2h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![American Airlines logo]()
$119
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:25 pm -
Nonstop2h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$119
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:18 pm -
1 stop4h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$129
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am -
1 stop4h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$129
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:20 am -
Nonstop2h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![United Airlines logo]()
$138
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:15 pm -
Nonstop2h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:15 am -
2 stops27h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$140
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:25 am -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![JetBlue logo]()
$142
This KAYAK deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/35:00 pm -
1 stop7h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![JetBlue logo]()
$143
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/203:16 pm -
1 stop8h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$146
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:06 pm -
1 stop5h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$148
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:00 pm -
1 stop6h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$148
Find flight deals from Vermont to Chicago
Keep the following information in mind while searching for Vermont to Chicago flight deals. Data was last updated September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $277 (Trip.com) |
One-way from | $119 (American Airlines) |
Popular in | January |
Cheapest in | May |
Average price | $319 |
Good round-trip deal | $358 or less |
Good one-way deal | $313 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Vermont to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 10, 2026.
Use the filters below to find and compare flights from Vermont to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
AlbanyChicago
ALB Albany Intl - ORD Chicago O'Hare Intl
ALBORD
Albany Intl
Wed 10/14
12:45 pm-2:19 pm
Nonstop2h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
Quickest round-trip
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Mon 10/26
7:15 pm-8:25 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
AlbanyChicago
ALB Albany Intl - ORD Chicago O'Hare Intl
ALBORD
Albany Intl
Thu 10/22
7:06 pm-11:57 pm
1 stop5h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Wed 10/21
6:10 am-11:54 am
1 stop6h 44m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Thu 10/1
6:00 am-9:07 am
1 stop4h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Wed 10/7
6:00 am-9:32 am
1 stop4h 32m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Sat 10/24
6:00 am-9:32 am
1 stop4h 32m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
HartfordChicago
BDL Hartford Bradley Intl - RFD Chicago Greater Rockford
BDLRFD
Hartford Bradley Intl
Wed 10/7
6:15 am-8:50 am
2 stops27h 35m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$140
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Tue 12/29
4:45 pm-6:43 pm
Nonstop2h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BurlingtonChicago
BTV Burlington - RFD Chicago Greater Rockford
BTVRFD
Burlington
Sat 10/3
9:53 am-9:18 am
2 stops24h 25m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Vermont to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Vermont with our price prediction graph.
ALB-ORD
ALB-MDW
BDL-RFD
BTV-ORD
BDL-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Vermont to Chicago
USVT-CHI
ALB-ORD
ALB-MDW
BDL-RFD
BTV-ORD
What is the cheapest month to book a flight from Vermont to Chicago?
Currently, May is the cheapest month in which you can book a flight from Vermont to Chicago (average of $311). Flying from Vermont to Chicago in February is currently the most expensive (average of $413). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from VT to CHI?
Find hourly flight availability from Vermont to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 10, 2026.
One of the essential ways to save on airfare from Vermont to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 75% on airfare.
Weekly flight availability from Vermont to Chicago
Explore weekly flight availability from Vermont to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 10, 2026.
The most flights from USVT to CHI are scheduled on a Tuesday (13 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Vermont to Chicago?
Airfare is typical for this route at the moment.
Vermont to Chicago flights typically cost between $279 and $409 in October.The cheapest round-trip price found within the last 5 days was $299 on United Airlines (Oct 22-Oct 25).
How far ahead should I book a flight from Vermont to Chicago?
Booking 84 days in advance of your planned departure date is, on average, the best time to get cheap flights from Vermont to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Related info for your journey
Find useful and relevant information for your journey from Vermont to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Vermont to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Vermont to Chicago by cabin class
Find flights from Vermont to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Vermont and Chicago flights
Browse other Vermont and Chicago flight options. Last updated on September 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Vermont to Chicago flights
Consider these flights traveling from Vermont to Chicago.
Top 2 airlines flying from Vermont to Chicago
Discover the top 2 airlines that operate flights from Vermont to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$360 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$239 | Average$347 | FlexibilityNo cancel fee | On-time71% |